CHE2060 2: Simple Structures, Functional Groups

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Presentation transcript:

CHE2060 2: Simple Structures, Functional Groups Topics Drawing molecular structures Arrow formalism & molecular framework Introduction to alkanes Isomers IUPAC naming of alkanes Alkyl halides & cycloalkanes Functional groups: where the action is Alkenes: hydrocarbons with > one double bond Alkynes: hydrocarbons with > one triple bond Alkene isomers: who’s across that double bond? Arenes Organohalogens Using molecular formulas Daley & Daley, Chapter 2 Organic Nomenclature & Functional Groups

Who’s across that double bond? Alkenes Isomers: Who’s across that double bond?

configurational isomers conformational isomers Types of isomers Same formula Different in some way isomers Same connectivity? no yes constitutional isomers stereoisomers Different single bond rotation? no yes configurational isomers conformational isomers mirror images? no yes diastereomers enantiomers & cis-trans or E-Z Karty p.177

Alkene steroisomers: cis vs. trans Because there is no rotation around double bonds, alkenes can form stereoisomers: substituents arranged differently on either side of the double bond. cis trans The two identical substituents are on the same side of the double bond The two identical substituents are on the opposite sides of the double bond cis-2-butene trans-2-butene Try cis-3-methyl-2-hexene. D&D, p.107-9

Retinal: cis-trans detection of light The retinal of the eye is exposed to light, detects that light, & transmits a signal (“light right there”) to the brain via the optic nerve. Retinal is the molecule responsible for detecting light and starting the signaling process. Exposure to light converts 11-cis-retinal to all trans-retinal. http://chemwiki.ucdavis.edu/Core/Biological_Chemistry/Photoreceptors/Chemistry_of_Vision/Cis-Trans_Isomerization_of_Retinal https://www.youtube.com/watch?v=r6v21W8zRIw H&P, p.13

Alkene carbons with non-identical groups? Cis and trans can be used to describe isomers only when each of the double bonded carbons share at least one substituent – like each has a methyl group. What if all four substituents are different? Identify the highest atomic mass atoms attached to each of the two double- bonded carbons. Determine whether the high mass atoms are on the same or opposite sides. Zussamen Entgegen High mass on the same side of the double bond High mass on the opposite side of the double bond E-4-ethyl-6,7-dimethyl-4-nonene E-3-cyclopentane-2-hexene D&D, p.107-9